Sodium Hydroxide → 1-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-1h-pyrazole-3-carboxylic acid

HRID 1505285Notes

Reaction equation

HRID 1505285 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[CH:8][N:7]([C:10]2[CH2:14][C:13]([C:19]3[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([Cl:26])[CH:20]=3)([C:15]([F:18])([F:17])[F:16])[O:12][N:11]=2)[N:6]=1)=[O:4].[OH-].[Na+]>C1COCC1.O>[Cl:25][C:23]1[CH:24]=[C:19]([C:13]2([C:15]([F:17])([F:16])[F:18])[O:12][N:11]=[C:10]([N:7]3[CH:8]=[CH:9][C:5]([C:3]([OH:4])=[O:2])=[N:6]3)[CH2:14]2)[CH:20]=[C:21]([Cl:26])[CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 584979901-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-1H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 584980431-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-1h-pyrazole-3-carboxylic acidYield 93.7%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of methyl ester of example 18.1 (408 mg) in 5 ml THF:water (4:1) was added sodium hydroxide (60 mg). The reaction was stirred 2 hours at room temperature before evaporation of the solvent in vacuo. The aqueous layer was extracted with ethyl acetate before being acidified. It was then extracted several times with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford the title acid (369 mg) as a yellowish solid. 1H-NMR (CDCl3, 400 MHz): 8.20 (s, 1H), 7.50 (m, 2H), 7.45 (m, 1H), 7.05 (s, 1H), 4.45 (d, 1H), 4.10 (d, 1H).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. extractionIt was then extracted several times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e890cb7e3aa446bbac957674c5b57192
Source dataset
uspto-grants-2015_12
Patent number
US09216973B2

Reaction notes

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